AU2004265311A1 - 2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds as CCK2 modulators - Google Patents

2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds as CCK2 modulators Download PDF

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Publication number: AU2004265311A1
Authority: AU; Australia
Prior art keywords: alkyl; phenyl; quinoxaline; group; carbonyl
Prior art date: 2003-08-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

AU2004265311A

Other languages

English (en)

Inventor

Brett D. Allison

Michael D. Hack

Victor K. Phuong

Michael H. Rabinowitz

Mark D. Rosen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceutica NV

Original Assignee

Janssen Pharmaceutica NV

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-08-08

Filing date

2004-08-04

Publication date

2005-02-24

2004-08-04 Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV

2005-02-24 Publication of AU2004265311A1 publication Critical patent/AU2004265311A1/en

Status Abandoned legal-status Critical Current

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GKXZNNBMEDANBL-UHFFFAOYSA-N 2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical class NC(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=NC=CN=C12 GKXZNNBMEDANBL-UHFFFAOYSA-N 0.000 title claims description 7
ARLKVQYMFRECLV-JSGCOSHPSA-N (2s)-2-[[(2s)-2-amino-3-(1h-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanamide Chemical compound C1=CC=C2C(C[C@H](N)C(=O)N[C@@H](CCSC)C(N)=O)=CNC2=C1 ARLKVQYMFRECLV-JSGCOSHPSA-N 0.000 title description 9
108091005932 CCKBR Proteins 0.000 title description 9
-1 hydroxy, fluoro, chloro, bromo, iodo Chemical group 0.000 claims description 278
125000000217 alkyl group Chemical group 0.000 claims description 247
229910052799 carbon Inorganic materials 0.000 claims description 147
150000001875 compounds Chemical class 0.000 claims description 132
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 128
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 95
125000005842 heteroatom Chemical group 0.000 claims description 70
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 58
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 49
NDGDQEAYECFDKQ-UHFFFAOYSA-N quinoxaline-5-sulfonic acid Chemical compound C1=CN=C2C(S(=O)(=O)O)=CC=CC2=N1 NDGDQEAYECFDKQ-UHFFFAOYSA-N 0.000 claims description 47
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 47
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 44
229910052757 nitrogen Inorganic materials 0.000 claims description 41
238000000034 method Methods 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 34
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000005605 benzo group Chemical group 0.000 claims description 31
150000001408 amides Chemical class 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
125000000623 heterocyclic group Chemical group 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 14
125000002541 furyl group Chemical group 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 14
125000001544 thienyl group Chemical group 0.000 claims description 14
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 11
208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
208000008469 Peptic Ulcer Diseases 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
150000004677 hydrates Chemical class 0.000 claims description 10
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
125000001475 halogen functional group Chemical group 0.000 claims description 7
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
201000002528 pancreatic cancer Diseases 0.000 claims description 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
208000019901 Anxiety disease Diseases 0.000 claims description 6
208000002193 Pain Diseases 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
230000036407 pain Effects 0.000 claims description 6
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
206010052747 Adenocarcinoma pancreas Diseases 0.000 claims description 5
206010009944 Colon cancer Diseases 0.000 claims description 5
206010061968 Gastric neoplasm Diseases 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
230000036506 anxiety Effects 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000003743 cholecystokinin B receptor antagonist Substances 0.000 claims description 5
208000029742 colonic neoplasm Diseases 0.000 claims description 5
108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 5
231100000029 gastro-duodenal ulcer Toxicity 0.000 claims description 5
201000002094 pancreatic adenocarcinoma Diseases 0.000 claims description 5
208000000689 peptic esophagitis Diseases 0.000 claims description 5
238000005897 peptide coupling reaction Methods 0.000 claims description 5
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 4
201000000052 gastrinoma Diseases 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
PNTRGJVDLKSGBN-UHFFFAOYSA-N (2-amino-4-bromophenyl)-(3,5-dimethylmorpholin-4-yl)methanone Chemical compound CC1COCC(C)N1C(=O)C1=CC=C(Br)C=C1N PNTRGJVDLKSGBN-UHFFFAOYSA-N 0.000 claims description 3
ZKFHWGMZDFARBB-UHFFFAOYSA-N (2-amino-4-bromophenyl)-morpholin-4-ylmethanone Chemical compound NC1=CC(Br)=CC=C1C(=O)N1CCOCC1 ZKFHWGMZDFARBB-UHFFFAOYSA-N 0.000 claims description 3
SHMSWAVVSXAJTM-UHFFFAOYSA-N (2-amino-4-chlorophenyl)-morpholin-4-ylmethanone Chemical compound NC1=CC(Cl)=CC=C1C(=O)N1CCOCC1 SHMSWAVVSXAJTM-UHFFFAOYSA-N 0.000 claims description 3
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
208000023514 Barrett esophagus Diseases 0.000 claims description 3
208000023665 Barrett oesophagus Diseases 0.000 claims description 3
208000030814 Eating disease Diseases 0.000 claims description 3
208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
206010017807 Gastric mucosal hypertrophy Diseases 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
208000031845 Pernicious anaemia Diseases 0.000 claims description 3
201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims description 3
235000014632 disordered eating Nutrition 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
HXQLYXWHNNLXRG-UHFFFAOYSA-N n-[4,5-dichloro-2-(morpholine-4-carbonyl)phenyl]quinoxaline-5-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC(NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)=C1C(=O)N1CCOCC1 HXQLYXWHNNLXRG-UHFFFAOYSA-N 0.000 claims description 3
JHAKBQPXDCQXEQ-UHFFFAOYSA-N n-[5-bromo-2-(1,3,4,5-tetrahydro-2-benzazepine-2-carbonyl)phenyl]quinoxaline-5-sulfonamide Chemical compound C1CCC2=CC=CC=C2CN1C(=O)C1=CC=C(Br)C=C1NS(=O)(=O)C1=CC=CC2=NC=CN=C12 JHAKBQPXDCQXEQ-UHFFFAOYSA-N 0.000 claims description 3
ACSGDPPWRUXBPD-UHFFFAOYSA-N n-[5-bromo-2-(piperidine-1-carbonyl)phenyl]quinoxaline-5-sulfonamide Chemical compound C=1C=CC2=NC=CN=C2C=1S(=O)(=O)NC1=CC(Br)=CC=C1C(=O)N1CCCCC1 ACSGDPPWRUXBPD-UHFFFAOYSA-N 0.000 claims description 3
LZAOGJRFUZULNT-CYBMUJFWSA-N n-[5-iodo-2-[(3r)-3-methylmorpholine-4-carbonyl]phenyl]quinoxaline-5-sulfonamide Chemical compound C[C@@H]1COCCN1C(=O)C1=CC=C(I)C=C1NS(=O)(=O)C1=CC=CC2=NC=CN=C12 LZAOGJRFUZULNT-CYBMUJFWSA-N 0.000 claims description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
JSOCEBRHMUZSHI-UHFFFAOYSA-N (2-amino-4-bromophenyl)-(3-methylmorpholin-4-yl)methanone Chemical compound CC1COCCN1C(=O)C1=CC=C(Br)C=C1N JSOCEBRHMUZSHI-UHFFFAOYSA-N 0.000 claims description 2
SIKPAQNIFOKIME-UHFFFAOYSA-N (2-amino-4-iodophenyl)-(3,5-dimethylmorpholin-4-yl)methanone Chemical compound CC1COCC(C)N1C(=O)C1=CC=C(I)C=C1N SIKPAQNIFOKIME-UHFFFAOYSA-N 0.000 claims description 2
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 2
125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 claims description 2
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
DKRZGORABOUMJH-CYBMUJFWSA-N 4-bromo-n-[(1r)-1-(2,4-dichlorophenyl)ethyl]-2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical compound C1([C@H](NC(=O)C=2C(=CC(Br)=CC=2)NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)C)=CC=C(Cl)C=C1Cl DKRZGORABOUMJH-CYBMUJFWSA-N 0.000 claims description 2
TZKCPFFVWLRNRZ-CYBMUJFWSA-N 4-bromo-n-[(1r)-1-(2,4-difluorophenyl)ethyl]-2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical compound C1([C@H](NC(=O)C=2C(=CC(Br)=CC=2)NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)C)=CC=C(F)C=C1F TZKCPFFVWLRNRZ-CYBMUJFWSA-N 0.000 claims description 2
DCKMBNDIHTZCNR-UHFFFAOYSA-N 4-bromo-n-[(4-chlorophenyl)methyl]-n-methyl-2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical compound C=1C=C(Br)C=C(NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)C=1C(=O)N(C)CC1=CC=C(Cl)C=C1 DCKMBNDIHTZCNR-UHFFFAOYSA-N 0.000 claims description 2
RMXHUTYQEVHIHC-UHFFFAOYSA-N 4-bromo-n-[1-(4-fluorophenyl)ethyl]-2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical compound C=1C=C(Br)C=C(NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)C=1C(=O)NC(C)C1=CC=C(F)C=C1 RMXHUTYQEVHIHC-UHFFFAOYSA-N 0.000 claims description 2
BXDMVVDKZNAMMX-CYBMUJFWSA-N 4-chloro-n-[(1r)-1-(2,4-difluorophenyl)ethyl]-2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical compound C1([C@H](NC(=O)C=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)C)=CC=C(F)C=C1F BXDMVVDKZNAMMX-CYBMUJFWSA-N 0.000 claims description 2
CKJIFPYCYCYRPW-UHFFFAOYSA-N 4-chloro-n-[1-(4-chlorophenyl)ethyl]-2-(quinoxalin-5-ylsulfonylamino)benzamide Chemical compound C=1C=C(Cl)C=C(NS(=O)(=O)C=2C3=NC=CN=C3C=CC=2)C=1C(=O)NC(C)C1=CC=C(Cl)C=C1 CKJIFPYCYCYRPW-UHFFFAOYSA-N 0.000 claims description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
229940022663 acetate Drugs 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 claims description 2
OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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ODLUSSYJGWHTCE-UHFFFAOYSA-N s-quinoxalin-5-yl n,n-diethylcarbamothioate Chemical compound C1=CN=C2C(SC(=O)N(CC)CC)=CC=CC2=N1 ODLUSSYJGWHTCE-UHFFFAOYSA-N 0.000 description 1
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238000012360 testing method Methods 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
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- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Ceramic Engineering (AREA)
Manufacturing & Machinery (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Materials Engineering (AREA)
Hematology (AREA)
Inorganic Chemistry (AREA)
Diabetes (AREA)
Structural Engineering (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Child & Adolescent Psychology (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

AU2004265311A 2003-08-08 2004-08-04 2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds as CCK2 modulators Abandoned AU2004265311A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US49407403P	2003-08-08	2003-08-08
US60/494,074		2003-08-08
PCT/US2004/025153 WO2005016896A1 (en)	2003-08-08	2004-08-04	2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds as cck2 modulators

Publications (1)

Publication Number	Publication Date
AU2004265311A1 true AU2004265311A1 (en)	2005-02-24

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ID=34193199

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Application Number	Title	Priority Date	Filing Date
AU2004265312A Expired - Fee Related AU2004265312B2 (en)	2003-08-08	2004-08-04	Process for the preparation of 2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds
AU2004265311A Abandoned AU2004265311A1 (en)	2003-08-08	2004-08-04	2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds as CCK2 modulators

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AU2004265312A Expired - Fee Related AU2004265312B2 (en)	2003-08-08	2004-08-04	Process for the preparation of 2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds

Country Status (33)

Country	Link
US (3)	US7304051B2 (de)
EP (2)	EP1651622B1 (de)
JP (2)	JP4818110B2 (de)
KR (1)	KR20060060007A (de)
CN (2)	CN1863782A (de)
AR (1)	AR045930A1 (de)
AT (2)	ATE353322T1 (de)
AU (2)	AU2004265312B2 (de)
BR (1)	BRPI0413449A (de)
CA (2)	CA2534887A1 (de)
CR (1)	CR8229A (de)
CY (1)	CY1106486T1 (de)
DE (2)	DE602004004663T2 (de)
DK (2)	DK1651621T3 (de)
EA (1)	EA200600203A1 (de)
EC (1)	ECSP066355A (de)
ES (2)	ES2281834T3 (de)
HR (1)	HRP20080559T3 (de)
IL (1)	IL173591A0 (de)
IS (1)	IS8280A (de)
LT (1)	LT5410B (de)
LV (1)	LV13453B (de)
MX (2)	MXPA06001550A (de)
NO (1)	NO20061122L (de)
NZ (1)	NZ545030A (de)
PL (2)	PL1651621T3 (de)
PT (2)	PT1651622E (de)
SG (1)	SG131114A1 (de)
SI (2)	SI1651621T1 (de)
TW (1)	TW200521120A (de)
UA (1)	UA84025C2 (de)
WO (2)	WO2005016897A1 (de)
ZA (1)	ZA200601946B (de)

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EP1651622B1 (de) *	2003-08-08	2007-02-07	Janssen Pharmaceutica N.V.	Verfahren zur herstellung von 2- (chinoxalin-5-ylsulfonylamino) -benzamid-verbindungen
WO2005085188A2 (en) *	2004-03-02	2005-09-15	Compass Pharmaceuticals Llc	Compounds and methods for anti-tumor therapy
WO2005105788A1 (en) *	2004-04-23	2005-11-10	Takeda San Diego, Inc.	Indole derivatives and use thereof as kinase inhibitors
US7947833B2 (en) *	2004-08-04	2011-05-24	Janssen Pharmaceutica Nv	Preparation of quinoxaline compounds
US7297816B2 (en) *	2004-09-24	2007-11-20	Janssen Pharmaceutica N.V.	Sulfonamide compounds
FR2904317A1 (fr)	2006-07-27	2008-02-01	Inst Nat Sante Rech Med	Analogues d'halogenobenzamides marques a titre de radiopharmaceutiques
US8592565B2 (en) *	2007-01-12	2013-11-26	The Board Of Trustees Of The Leland Stanford Junior University	Preparation of azide-modified carbon surfaces for coupling to various species
JP5497429B2 (ja)	2007-03-07	2014-05-21	武田薬品工業株式会社	ベンゾオキサゼピン誘導体およびその用途
WO2008124518A1 (en) *	2007-04-03	2008-10-16	Janssen Pharmaceutica N.V.	Oxo-dihydroisoindole sulfonamide compounds as modulators of the cck2 receptor
EP2131245A3 (de) *	2008-06-02	2012-08-01	ASML Netherlands BV	Lithografische Vorrichtung und deren Fokusbestimmungsverfahren
WO2009154754A2 (en) *	2008-06-17	2009-12-23	Concert Pharmaceuticals, Inc.	Synthesis of deuterated morpholine derivatives
US20100305093A1 (en) *	2009-04-09	2010-12-02	Exelixis, Inc.	Inhibitors of mTOR and Methods of Making and Using
EP2486004B1 (de)	2009-10-09	2017-05-03	Zafgen, Inc.	Sulfonverbindungen zur verwendung in der behandlung von adipositas
EP2590953B1 (de)	2010-07-09	2014-10-29	Convergence Pharmaceuticals Limited	Tetrazolverbindungen als calciumkanalblocker
CA2806221A1 (en)	2010-07-22	2012-01-26	Zafgen, Inc.	Tricyclic compounds and methods of making and using same
EP2668169B1 (de)	2011-01-26	2017-11-15	Zafgen, Inc.	Tetrazolverbindungen sowie verfahren zu ihrer herstellung und verwendung
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2004
- 2004-08-04 EP EP04780056A patent/EP1651622B1/de not_active Expired - Lifetime
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Also Published As

Publication number	Publication date
PL1651621T3 (pl)	2009-01-30
JP2007501842A (ja)	2007-02-01
BRPI0413449A (pt)	2006-10-17
TW200521120A (en)	2005-07-01
SI1651621T1 (sl)	2008-12-31
CR8229A (es)	2008-09-10
CN1863781A (zh)	2006-11-15
ZA200601946B (en)	2007-05-30
DK1651621T3 (da)	2008-11-10
CY1106486T1 (el)	2012-01-25
PL1651622T3 (pl)	2007-07-31
DE602004004663T2 (de)	2007-11-22
HRP20080559T3 (hr)	2009-01-31
JP2007501841A (ja)	2007-02-01
SG131114A1 (en)	2007-04-26
US7563895B2 (en)	2009-07-21
US7288651B2 (en)	2007-10-30
MXPA06001482A (es)	2006-09-04
JP4818110B2 (ja)	2011-11-16
DE602004004663D1 (de)	2007-03-22
ES2281834T3 (es)	2007-10-01
UA84025C2 (en)	2008-09-10
WO2005016897A1 (en)	2005-02-24
WO2005016896A1 (en)	2005-02-24
NZ545030A (en)	2009-08-28
US20080076918A1 (en)	2008-03-27
ATE403650T1 (de)	2008-08-15
PT1651622E (pt)	2007-04-30
CN1863782A (zh)	2006-11-15
EP1651622B1 (de)	2007-02-07
DK1651622T3 (da)	2007-05-07
SI1651622T1 (sl)	2007-06-30
EP1651621A1 (de)	2006-05-03
ATE353322T1 (de)	2007-02-15
PT1651621E (pt)	2008-09-30
NO20061122L (no)	2006-05-04
ES2310294T3 (es)	2009-01-01
IS8280A (is)	2006-01-31
AU2004265312A1 (en)	2005-02-24
US7304051B2 (en)	2007-12-04
ECSP066355A (es)	2006-08-30
CA2534887A1 (en)	2005-02-24
CA2534885C (en)	2013-06-04
AR045930A1 (es)	2005-11-16
CA2534885A1 (en)	2005-02-24
EA200600203A1 (ru)	2006-08-25
EP1651622A1 (de)	2006-05-03
IL173591A0 (en)	2006-07-05
DE602004015614D1 (de)	2008-09-18
MXPA06001550A (es)	2006-09-04
US20050038032A1 (en)	2005-02-17
EP1651621B1 (de)	2008-08-06
KR20060060007A (ko)	2006-06-02
US20050043310A1 (en)	2005-02-24
AU2004265312B2 (en)	2010-05-20
LT5410B (lt)	2007-03-26
LV13453B (en)	2007-02-20
LT2006017A (en)	2006-11-27

Publication	Publication Date	Title
AU2004265312B2 (en)	2010-05-20	Process for the preparation of 2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds
US7550492B2 (en)	2009-06-23	Benzo[1,2,5]thiadiazole compounds
US7947833B2 (en)	2011-05-24	Preparation of quinoxaline compounds
JPWO1994014796A1 (ja)	1995-02-02	新規なｎ−（ピリジルカルボニル）ベンズアゼピン誘導体及びその中間体

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